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- Title
Multiple Halogenation of Aliphatic C−H Bonds within the Hofmann–Löffler Manifold.
- Authors
Del Castillo, Estefanía; Martínez, Mario D.; Bosnidou, Alexandra E.; Duhamel, Thomas; O'Broin, Calvin Q.; Zhang, Hongwei; Escudero‐Adán, Eduardo C.; Martínez‐Belmonte, Marta; Muñiz, Kilian
- Abstract
An innovative approach to position‐selective polyhalogenation of aliphatic hydrocarbon bonds is presented. The reaction proceeded within the Hofmann‐Löffler manifold with amidyl radicals as the sole mediators to induce selective 1,5‐ and 1,6‐hydrogen‐atom transfer followed by halogenation. Multiple halogenation events of up to four innate C−H bond functionalizations were accomplished. The broad applicability of this new entry into polyhalogenation and the resulting synthetic possibilities were demonstrated for a total of 27 different examples including mixed halogenations. More than one at a time! Multiple site‐selective C−H halogenation events can be accomplished as an innovative variant of the classic Hofmann–Löffler reaction by using halogenated hydantoins as oxidant and halide source. The reaction scope includes cyclic and linear hydrocarbons, as well as vicinal and geminal halogenation.
- Subjects
HALOGENATION; CARBON-hydrogen bonds; ALIPHATIC compounds; AMIDYL radicals; OXIDIZING agents
- Publication
Chemistry - A European Journal, 2018, Vol 24, Issue 65, p17225
- ISSN
0947-6539
- Publication type
Academic Journal
- DOI
10.1002/chem.201804504